This week’s episode is one of those conversations that sticks with you. We sat down with Scott Leese, a name you might know from LinkedIn, Surf & Sales, or any of the six (!) unicorns he’s helped build. But behind the “sales whisperer” reputation is a guy who’s survived nine surgeries, beat an opioid dependency, and still shows up every day with more urgency than most twenty-somethings trying to break into tech.

Scott doesn’t just talk about hustle; he talks about pain. About walking away from easy money when it started to feel fake. About pulling the ripcord on corporate life the moment a 24-year-old founder told him he couldn’t leave work early for his kid’s little league game. About cold plunges, trauma, and why authenticity is the only thing that scales.

It’s raw. It’s inspiring. And it’s a reminder that the edge you think you’re grinding for might already be in you, sharpened by the things you’ve endured, not the titles on your resume or LinkedIn profile.

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In 2024, Scott was making thousands of dollars per sponsored LinkedIn post. That’s not hyperbole, one post, multiple thousands, often enough to stack to $10K or more in a month. Easy money. But it didn’t sit right.

At first, endorsing products felt fine when he liked the founder or believed in the tool. But slowly, it got icky. Some of the vendors wanted to control his tone. They’d hire him for his voice, then try to rewrite him into someone else. And some followers started calling him out: “Do you actually use this?” That’s when he realized the slope he was sliding down.

So at the start of 2025, he cut it off. No more paid posts. He walked away from a nice chunk of income because not all dollars are good dollars. And the honesty in that decision, that pre-emptive guardrail before losing himself—it’s a lesson for anyone trying to build a personal brand without letting the brand hollow you out.

But authenticity didn’t just come from LinkedIn lessons. It was forged in pain—literal, physical pain.

Back in his twenties, Scott’s life unraveled. He was in grad school, pulling double duty teaching undergrad courses while compressing a two-year master’s into one. Stress caught up. Out of nowhere, his health collapsed. He dropped sixty pounds in two months. Doctors diagnosed him with severe ulcerative colitis.

What followed was years of hell: nine surgeries, four of them life-saving. Emergency leaks, blockages, growths, constant pain. Pre-Netflix, pre-social media, which meant isolation in the truest sense—just you, the hospital bed, and whatever demons crawl out when you’re alone too long.

Pain meds helped until they didn’t. By the time he clawed his way back to “healthy,” he had an opioid dependency. Cold turkey was the only way forward. Against doctor’s orders, he signed papers waiving liability and went through it. Think Trainspotting, but without the movie glamour.

And when he came out the other side, he was 27, degree in hand, but no clear future. A friend nudged him into sales. Early 2000s startups didn’t care about experience—they just needed bodies. He jumped in. Competitive fire, resilience, a psychology background, and the perspective that “quota isn’t life or death” carried him. Compared to what he’d been through, a missed sales target wasn’t going to break him. That urgency, that perspective—it became his edge.

The thing about trauma, though, is it doesn’t leave. Scott admits: his version of “healthy” would send most of us back to the ER. He still deals with pain every day. He takes multiple meds. He has to get checked constantly. And hanging over it all is the looming shadow of life expectancy statistics—people with his condition average early sixties. Scott’s 48 now. Do the math, and the thought creeps in: Do I only have 10, 15 years left?

That’s not just numbers—that’s fear. Fear of leaving his kids without a father too soon. Fear of the rug being pulled out again. It fuels him, but it also scars him.

So he’s built rituals: daily cold plunges in the Austin heat, a backyard sauna, a diet stripped of forty-plus allergens, grounding practices that balance body and mind. They’re part health, part therapy, part anchor. He admits he still struggles with “all gas or all stop.” He distracts himself from pain by staying busy, sometimes too busy. But over time, he’s found moments of a sweet spot—something closer to balance. Not perfect, but progress.

When Scott works with startups now, he brings that lens. He’s not just looking at sales scripts or ops processes. He’s watching for urgency in the founders—because urgency reveals itself in little ways. How fast do they reply? How long do they take to hire? Do they execute, or do they debate endlessly?

He’s picky about clients. If a founder won’t take feedback, if they want to argue instead of implement, if their market’s too small—he’s not interested. He’s looking for unicorn potential, not mediocrity. Because at this stage, he doesn’t need the check—he needs the challenge.

Going out on his own wasn’t quick or easy. Friends pushed him years earlier, but he waited. He had young kids. Health issues. And he hadn’t had that unicorn win yet. So he kept grinding VP of Sales roles until his consulting side income matched his W-2. At one point, he was making $400K plus stock. He wrote books, built communities like Surf & Sales, stacked side projects. Then he helped scale a company from zero revenue to a billion-dollar valuation. That was the signal: time to bet on himself.

But the breaking point wasn’t just financial. It was personal. After making his founder a billionaire, Scott asked to leave a little early for his kid’s little league game. The 24-year-old CEO told him no. That’s when he knew: life was too short. He pulled the ripcord and never looked back.

Ask Scott if he feels accomplished, and he hesitates. Proud? Yes. Accomplished? Not yet. He’s close, but still hungry. He’s launched a landscaping business in Austin because he realized his portfolio had nothing in trades—industries safe from AI for now. He can’t stop stacking income streams, building experiments. But he also admits he wrestles with comparison, with jealousy, with the mental tug-of-war between stoicism and pettiness. He’s not above being human.

The advice he leaves behind is simple, though: optimize for action. Don’t overthink. Shrink the gap between idea and execution. Publish the post even if it’s messy. Start the business even if the Instagram page is empty. Quit the job if you know it’s time. Waiting rarely makes the leap easier.

Scott’s story of urgency and action isn’t just anecdotal wisdom. Research shows that adversity often forges resilience and motivation. A longitudinal study by Seery et al. (2010) found that individuals who had endured moderate lifetime adversity showed better mental health, higher well-being, and greater life satisfaction than those with either no adversity or extreme adversity. In other words: the very struggles that nearly broke him became the foundation of his drive.

Listening to Scott, you realize the hustle and the hospital aren’t separate stories—they’re the same one. The fight to recover built the grit to sell. The scars shaped the urgency. The authenticity comes not from theory but from survival.

And maybe that’s the real takeaway: success isn’t just about how fast you can scale, or how many followers you stack. It’s about knowing what’s real, protecting it fiercely, and refusing to sell yourself short—even if it means walking away from easy money or telling a billionaire founder you’re going to your kid’s game.

Because life is short. Too short for fake endorsements. Too short for missed little league games. Too short to be anything but authentic.

—Troy & Daniel

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